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438 Holiday Party Entertainers serving Chelsea, MA

Featured

Dan Alan Levine Music

5.0 (6)
Top Performer
18 Verified bookings

  • Boston, MA
  • Pianist / Holiday Party Entertainment
  • 3 miles from Chelsea
  • $325 – $2,500 per event

Maher D. said “Dan did an amazing job for our wedding. He is extremely talented, responsive, and punctual. He communicated in advance to know exactly what we wanted. We asked for a few specific things and let him...”
Featured

NewBartenders

5.0 (2)
Top Performer
3 Verified bookings

  • Boston, MA
  • Bartender / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Starts at $500

Kristina F. said “Hired for a birthday party and everyone loved it! So much talent - and such a conversation starter! Great way to turn up the volume on an event”
Featured

Matt Roberts: Clean Comedy Magic

5.0 (74)
Top Performer
120 Verified bookings

  • Boston, MA
  • Magician / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Contact for pricing

Raymond R. said “The kids had a great time and were eager to be called onto stage! He was funny and had good magic tricks :)”
Featured

Shadowbreeze

5.0 (2)
Top Performer
3 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Contact for pricing

Lucy T. said “They played at a 1920s themed party I had organized and they were incredible! Well prepared, on time, kind, and very talented. I would highly recommend!”
Featured

AJ Piano Works - Restaurant, Bar, & Hotel Lounge Pianist & Singer

5.0 (17)
Top Performer
24 Verified bookings

  • Boston, MA
  • Pianist / Holiday Party Entertainment
  • 3 miles from Chelsea
  • $200 – $800 per event

Jackie L. said “AJ was INCREDIBLE!!! He is so talented and such a pleasure to work with. He arrived an hour prior to the event to warm up on the piano. The residents and guests loved listening to him. We will...”
Featured

Chandler Boston Magician

5.0 (11)
Top Performer
15 Verified bookings

  • Boston, MA
  • Magician / Holiday Party Entertainment
  • 3 miles from Chelsea
  • $500 – $2,000 per event

Penni M. said “Chandler was fantastic. My guests loved him.”
Featured

The Creswell Club

5.0 (32)
Top Performer
43 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Starts at $1,200 per hour

Alexa said “Dan & Creswell club we’re absolutely amazing! Due to Covid, plans had to be altered many times and they were all so accommodating and went with it! We received so many compliments from our guests as...”
Featured

D'Amico Entertaintainment

5.0 (88)
Top Performer
45 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Contact for pricing

John B. said “Excellent communication throughout the process. Violinist was excellent and performed all the requested songs perfectly. This was absolutely worth every penny.”
Featured

Gerry Beaudoin Trio

4.97 (40)
Top Performer
59 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Chelsea
  • $250 – $5,000 per event

Whit B. said “Really loved chatting with Gerry. He is such a nice guy and his music was perfect for our event. I would 10 out of 10 hire him again!”
Featured

Jazz Breeze

5.0 (29)
Top Performer
47 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Contact for pricing

Richard said “Jazz Breeze were great to deal with and get all the plans in place for a last minute event. The musician were so good and perfect for the atmosphere we were trying to create at the event. Thank You.”
Featured

Santa Bob

5.0 (11)
Top Performer
14 Verified bookings

  • Mattapan, MA
  • Santa Claus / Holiday Party Entertainment
  • 8 miles from Chelsea
  • Starts at $200

Lisa B. said “Santa Bob has come to our home for the past few years. He is so personable and he looks exactly like the “real” Santa! He is patient and engaging and I’d recommend him for any event you need...”
Featured

Gillian Berkowitz

5.0 (48)
Top Performer
58 Verified bookings

  • Natick, MA
  • Pianist / Holiday Party Entertainment
  • 18 miles from Chelsea
  • Starts at $500

Amy S. said “Gillian was so wonderful! Her playing was delightful and warm and set the perfect tone for our intimate holiday party. Would highly recommend!”
Featured

Great Scott Productions

4.82 (77)
Top Performer
160 Verified bookings

  • Rockland, MA
  • Magician / Holiday Party Entertainment
  • 19 miles from Chelsea
  • Starts at $100

Joel F. said “Grat Scott providing a hilarious show for my friends and I - wholly recommend.”
Featured

Santa Ross

5.0 (6)
Top Performer
19 Verified bookings

  • Marshfield, MA
  • Santa Claus / Holiday Party Entertainment
  • 27 miles from Chelsea
  • Starts at $250

Gira W. said “He was awesome. ”
Featured

Santa Grande

5.0 (7)
Top Performer
16 Verified bookings

  • Salem, NH
  • Santa Claus / Holiday Party Entertainment
  • 29 miles from Chelsea
  • $200 – $350 per hour

Nell H. said “Santa Grande was on time, professional and lovely to chat with both in character and out. Would recommend for any of your booking needs! ”
Featured

Santa Dan

4.99 (104)
Top Performer
268 Verified bookings

  • Taunton, MA
  • Santa Claus / Holiday Party Entertainment
  • 34 miles from Chelsea
  • $175 – $1,000 per event

Courtney W. said “Santa Dan is the best!!! Kids loved him!!!”
Featured

SpeechLess

4.98 (21)
2 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Chelsea
  • $3,500 – $25,000 per event

Emma M. said “Speechless was an amazing addition to our wedding! They mastered the custom songs and were such a fun part of the cocktail hour. I highly highly recommend them!”
Featured

Mega Magic- Magician Mike D'Urzo

5.0 (23)
23 Verified bookings

  • Boston, MA
  • Magician / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Contact for pricing

Graham W. said “Mike was a great entertainer and showman who greatly elevated our event!”
Featured

The Christmas Carolers, LLC

4.78 (14)
61 Verified bookings

  • Boston, MA
  • Christmas Carolers / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Contact for pricing

Richard V. said “The group was fantastic! We thoroughly enjoyed their caroling and would highly use and recommend them again!”
Featured

Morgan Treni & The Golden Estate House Band

5.0 (17)
1 Verified booking

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Starts at $2,500

Abbey K. said “It is without any reservation that I recommend The Golden Estate House Band. Morgan and company created a magical experience for my wedding ceremony, cocktail party, dinner, and reception. Morgan...”
Featured

Holiday Victorian Carolers

4.91 (34)
65 Verified bookings

  • Boston, MA
  • Christmas Carolers / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Contact for pricing

Cheryl L. said “The Holiday Victorian Carolers made a surprise visit to my brother’s private Christmas Party in Ipswich, Massachusetts. He and the 40 guests were so surprised and delighted with their remarkable...”
Featured

Louis Pettinelli Entertainment

4.92 (70)
249 Verified bookings

  • Boston, MA
  • Jazz Band / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Starts at $300

Alayna B. said “We hired Louis Pettinelli Entertainment for a trio including a violin, piano, and cello for our wedding reception and they did such an amazing job! They really made the evening so special. They played...”
Featured

Marvelous Santas

4.99 (57)
102 Verified bookings

  • Saugus, MA
  • Santa Claus / Holiday Party Entertainment
  • 5 miles from Chelsea
  • $50 – $400 per event

Rosemary F. said “Would hire him again :)”
Featured

Exquisite Event Services

4.76 (78)
144 Verified bookings

  • Arlington, MA
  • Bartender / Holiday Party Entertainment
  • 7 miles from Chelsea
  • Contact for pricing

Sandra S. said “Wonderful service - Katherine was on time, helpful and proactive. Having her there allowed us to enjoy our party. Thank you!”
Featured

Todd Brunel Musical Groups

5.0 (4)
6 Verified bookings

  • Arlington, MA
  • Jazz Band / Holiday Party Entertainment
  • 7 miles from Chelsea
  • Starts at $200

Natasha B. said “Todd and his group played at a nonprofit gala we planned. He was responsive, listened to our requests and easy to work with! ”
Featured

GL3 Magic

5.0 (1)
1 Verified booking

  • Shrewsbury, MA
  • Magician / Holiday Party Entertainment
  • 35 miles from Chelsea
  • Contact for pricing

Alyssa M. said “Isaac was great for our annual Halloween Party! His communication, timeliness and willingness to be flexible are to be commended. We had mainly teenagers and parents, and he truly astounded all with...”
Featured

Santa Gary

5.0 (5)
7 Verified bookings

  • Leominster, MA
  • Santa Claus / Holiday Party Entertainment
  • 38 miles from Chelsea
  • Starts at $150 per hour

Joy R. said “We had a party of about 40 people at our house. A mix of adults, teenagers and little ones. Santa was very responsive and great at figuring out what we needed for our event. He looks very professional...”
Featured

  • Boston, MA
  • Bartender / Holiday Party Entertainment
  • 3 miles from Chelsea
  • Starts at $450

Copa Mobile Bar delivers a fully customizable bar experience to events across New England. From elegant weddings to lively corporate parties and intimate...
Featured

Munsey's Magic

5.0 (84)

  • Medford, MA
  • Magician / Holiday Party Entertainment
  • 4 miles from Chelsea
  • Contact for pricing

Lauren M. said “Jim was absolutely amazing for my friend’s bachelorette party. He had even the most skeptical of our friends stunned. I can’t express how good he was! I would absolutely hire him again in the future.”
Featured

  • Littleton, MA
  • Magician / Holiday Party Entertainment
  • 26 miles from Chelsea
  • Contact for pricing

I use the art of magic to bring wonder, laughter, and memorable moments to audiences of all ages. From children’s birthday parties to strolling magic at...
Featured

  • Cumberland, RI
  • Santa Claus / Holiday Party Entertainment
  • 35 miles from Chelsea
  • $100 – $150 per hour

Debra B. said “Soul Santa Solomon For three years, Soul Santa Solomon has been the heartbeat of the National Black Doll Museum’s **Ebony Village**, bringing joy to children and adults alike. With his radio...”

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About booking Holiday Party Entertainment in Chelsea, MA

The holidays offer special opportunities to create joy and connection with people you care about the most, and the right entertainment can make your celebration truly shine. From Christmas carolers setting a festive mood to Santas delighting children or DJs keeping the dance floor busy, professional entertainers bring the magic that makes a party memorable. Whether you’re planning a large corporate holiday party or a cozy family Christmas party, you can find the right performer to help you create unforgettable moments.

The cost of hiring holiday party entertainers in Chelsea, Massachusetts will vary depending on the type of holiday entertainment, their experience, and the length of the performance. A short Santa visit at your family Christmas party will cost less than a live band performing at a holiday corporate event. Contact the local entertainers above to discuss your event details and receive a customized quote.

As you search for Chelsea holiday party entertainers, view their profiles to read about their services, browse photos, and watch promotional videos. Then, check out reviews from past clients to see what it would be like to work with them. When requesting a quote, include key details like the venue, audience size, expected performance time, and event goals to ensure you receive the most accurate pricing.

Once you find the holiday act you want to hire, finalize the booking on GigSalad. Our full-service platform makes it easy to book holiday party entertainers. You can message the performers, confirm the details of your agreement, and make a secure payment all in one place. Every GigSalad event is covered by our Worry-Free Guarantee, so you can rest easy knowing we’ve got your back. Just relax and let the holiday magic unfold!

Holiday Party Entertainment serving the Chelsea, MA area

These Holiday Party Entertainment serve the wider Chelsea and Suffolk county area and travel to East Boston, Revere, Everett, Charlestown, Boston, Winthrop, Malden, Somerville, Cambridge, Medford, Melrose, Saugus, Roxbury Crossing, New Town, West Medford, Allston, Brookline Village, Roxbury, Brookline, Nahant, Dorchester, Arlington, Lynn, Winchester, Stoneham, Jamaica Plain, Dorchester Center, Brighton, Belmont, and Waverley.

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